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US7001880B1 - Method of collection of fragrance ingredient, perfume composition containing this fragrance ingredient and cosmetics containing this fragrance ingredient - Google Patents

Method of collection of fragrance ingredient, perfume composition containing this fragrance ingredient and cosmetics containing this fragrance ingredient Download PDF

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Publication number
US7001880B1
US7001880B1 US09/857,618 US85761801A US7001880B1 US 7001880 B1 US7001880 B1 US 7001880B1 US 85761801 A US85761801 A US 85761801A US 7001880 B1 US7001880 B1 US 7001880B1
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United States
Prior art keywords
fragrance
collection
fragrance ingredient
ingredient
extract
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US09/857,618
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English (en)
Inventor
Katsuyuki Yomogida
Seiichi Hirose
Masanori Yoshimura
Hitoshi Harigae
Masayuki Kataoka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Soda Aromatic Co Ltd
Shiseido Co Ltd
Original Assignee
Soda Aromatic Co Ltd
Shiseido Co Ltd
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Application filed by Soda Aromatic Co Ltd, Shiseido Co Ltd filed Critical Soda Aromatic Co Ltd
Assigned to SHISEIDO CO., LTD. reassignment SHISEIDO CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HARIGAE, HITOSHI, KATAOKA, MASAYUKI, HIROSE, SEIICHI, YOMOGIDA, KATSUYUKI, YOSHIMURA, MASANORI
Assigned to SODA AROMATIC CO., LTD. reassignment SODA AROMATIC CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: HARIGAE, HITOSHI, KATAOKA, MASAYUKI, HIROSE, SEIICHI, YOMOGIDA, KATSUYUKI, YOSHIMURA, MASANORI
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/027—Recovery of volatiles by distillation or stripping
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/02—Recovery or refining of essential oils from raw materials
    • C11B9/025—Recovery by solvent extraction

Definitions

  • the present invention relates to an improved method of collection a fragrance ingredient and a perfume composition containing the fragrance ingredient and a cosmetic containing the fragrance ingredient.
  • the invention provides an improvement of the fragrance quality of a perfume composition containing the fragrance ingredient.
  • the invention provides an improvement of the fragrance quality of a cosmetic containing the fragrance ingredient.
  • An agarwood is the fragrant wood containing the resin that has unique aroma.
  • the producing district of agarwood is found mainly in Southeast Asia.
  • the fragrance of the agarwood obtained by heating or burning was used as incense.
  • the high quality agarwood called “Kyara”, is highly prized.
  • the collection method of fragrance ingredient from a fragrant wood is by the thermal decomposion of the fragrant wood powder with a mixed gas as described in Japanese Unexamined Patent Publication No. Hei 6-93287.
  • this collection method had a disadvantage that a burnt smell depending on the dry distillation of fragrant wood can not be removed.
  • this method is a complicated method that requires a special apparatus and an adjustment of heating temperature and mixed gas.
  • the decomposition product of fragrant wood yields ingredient other than original fragrance ingredient and the colored solution. Therefore, it was impossible to reproduce the original aroma of agarwood completely from the collected fragrance ingredient of the prior art.
  • An object of the present invention is to provide a method that collects only desirable fragrance ingredient effectively without a burnt smell. It is an object to reproduce the original aroma of fragrant wood from fragrant wood. It is further object of the present invention is to provide an application of the original aroma fragrance ingredient to the various fragrance products and cosmetics.
  • a method of collection of a fragrance ingredient of the present invention comprises extracting the essential oil ingredient by solvent from a fragrant wood and collecting the fragrance ingredient in vapor-phase by heating the extract.
  • said fragrance ingredient is discharged forcibly from a heating container by introducing an inert gas.
  • said fragrance ingredient is collected to an absorption solvent and get a resultant as a fragrance collection liquid.
  • said fragrant wood is agarwood.
  • a perfume composition of the present invention contains said fragrance ingredient by means of the method of collection of the fragrance ingredient.
  • said perfume composition contains a fragrant wood extract.
  • a ratio of the fragrance collection solution/said fragrant wood extract is 0.25 to 9.
  • said perfume composition of the present invention it is preferable that said perfume composition has an aroma of agarwood.
  • a cosmetic of the present invention contains said fragrance ingredient by means of the method of collection of the fragrance ingredient.
  • said cosmetic contains a fragrant wood extract.
  • a ratio of the fragrance collection liquid/said fragrant wood extract is 0.25 to 9.
  • FIG. 1 shows one example of the fragrance collection apparatus that is used for the present invention.
  • Powder or chips of fragrant wood is processed by heating agitation extraction or by soaking extraction for extracting the essential oil ingredient. After filtering, the extract is obtained by removing the solvent. This extract is heated and the volatized fragrance in the head space is led outside the system. The introduction of inert gas is more suitable.
  • the fragrance ingredient is collected in an absorption solvent which becomes a fragrance collection liquid.
  • the perfume composition containing this fragrance collection liquid can reproduce the original fragrance of the fragrant wood.
  • the cosmetic containing this fragrance collection liquid can improve the quality of aroma.
  • the powder or the pieces of the fragrant wood can be used suitably as a fragrant wood material.
  • the fragrant wood in the present invention is a agarwood or a sandalwood etc.
  • the agarwood is grouped into 6 kinds which is called “Rikkoku”.
  • “Rikkoku” is derived from producing district of the fragrant wood, i.e. “Kyara”, “Rakoku”, “Manaban”, “Manaka”, “Sasora”, “Sumotara” etc. Many of the fragrant woods are produced from the hinterland of Vietnam, Cambodia and Srivasza. However, the differentiation of a producing district becomes meaningless now. The quality of tree is decided on the basis of the figure and aroma of fragrant wood.
  • a solvent is used to extract the essential oil ingredient containing the fragrance ingredient in the fragrant wood in the present invention.
  • Water, methanol, ethanol, isopropanol, diethylether, pentane, hexane, propyleneglycol, glycerin etc. or these mixture solvent etc. are used for the solvent that extracts the essential oil ingredient containing the fragrance ingredient of the fragrant wood.
  • a desirable process that extracts the essential oil ingredient which contains ingredients from fragrant wood is, for example, the extraction processing in 3 to 6 hours at 40° C. to 60° C. using heating extraction with agitation. Also, for example, it is desirable to extract for 1 to 10 days at room temperature using soaking extraction.
  • the crude extract (the essential oil ingredient) that is obtained is treated with solid-liquid separation by the optional method such as filtration or centrifugation.
  • the separated liquid that is obtained is concentrated and the extract is obtained.
  • the concentration method of the separated liquid for example, the method of public knowledge can be used, such as distilling and removing solvent under reduced pressure by the rotary evaporator.
  • the concentration extract that is obtained by the above described process is inserted into the fragrance collection apparatus.
  • the fragrance ingredient volatilized by heating is discharge forcibly through collection apparatus by the aeration of an inert gas, and is collected to the absorption solvent inside the collection apparatus.
  • FIG. 1 shows one example of the fragrance collection apparatus that is used to the collection method of the fragrance ingredient of the present invention.
  • the concentrated extraction liquid is heated in the heating container 1 together with an inert gas introduced through introduction pipe 2 .
  • the fragrance ingredient volatilizes in heating container 1 .
  • the fragrance ingredient with the inert gas that is introduced from introduction pipe 2 which passes through the connection pipe 3 is introduced to the collection apparatus 4 , and is collected in absorption solvent 5 .
  • an agitation apparatus can be attached to the heating container 1 .
  • a drum style container or a flask style container as the heating container, it can also be heated with rotation.
  • the collection apparatus can use either countercurrent contact style or batch style.
  • fragrance ingredient that was collected in this way is preserved as the fragrance collection liquid which contains the fragrance ingredient.
  • a perfume composition can contain the fragrance collection liquid combined with another perfume in optional proportion.
  • the perfume composition in the present invention includes any product that is the perfume fragrance with except for food mainly, for example perfume, colon, bath agents, various kinds cleaners, sanitation articles, incense sticks, aromatics etc.
  • an improved more excellent aroma of fragrant wood can be obtained.
  • the manufacturing method of extract of the fragrant wood is sufficient with the method of public knowledge.
  • a ratio by weight of fragrance collection liquid/fragrant wood extract is preferably approximately 0.25 to 9. In the case that this ratio missed, the original fragrance of fragrant wood may be damaged.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 180° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the solvent that extracts fragrant wood was changed into methanol, and the extraction processing of the method similar to Working example 1 was carried out.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 180° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the solvent that extracts fragrant wood was changed into 95% ethanol, and the extraction processing of the condition similar to Working example 1 was carried out and the extract was obtained by removing the solvent.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 180° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 m/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the solvent that extracts fragrant wood was changed into hexane, and the extraction processing of the condition similar to Working example 1 was carried out and the extract was obtained by removing the solvent.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 180° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the extraction processing of fragrant wood was carried out with diethyl ether and the extract was obtained by removing the solvent.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 150° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the extraction processing of fragrant wood was carried out with diethyl ether and the extract was obtained by removing the solvent.
  • the extract oil was transferred to Claisen flask type distillation apparatus, was heated to 200° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min. The fragrance ingredient was collected for 60 minutes. In the collection method, 30 ml of 95% ethanol was used as absorption solvent. The distilled fragrance ingredient with the gas was collected in the absorption solvent by a introducing tube whose exit was in the absorption solvent. The collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • An dry distillated collection liquid was obtained from the fragrant wood powder by dry distillation with the apparatus similar to Working example 1.
  • the extract oil was transferred to Claisen flask type distillation apparatus, and it was heated to 180° C. with an oil bath. Nitrogen gas was introduced with flow rate of 300 ml/min.
  • the fragrance ingredient was collected for 60 minutes.
  • 30 ml of 95% ethanol was used as absorption solvent.
  • the distilled fragrance ingredient with the gas was collected in the absorption solvent by an introducing tube whose exit was in the absorption solvent.
  • the collection apparatus was connected in series (30 ml ⁇ 2) and the fragrance ingredient volatilized was collected. Considering increasing collection efficiency, the absorption solvent was cooled with an ice water bath.
  • the dry distillation collection liquid that was collected was compared with Working example 1 of the present invention method.
  • Table 1 and Table 2 show the result of the extraction process with regard to Working examples 1 to 6 and Comparative example 1.
  • Table 3 shows the parameters of the methods of the heating fragrance collection process with regard to Working examples 1 to 6 and Comparative example 1.
  • Table 4 shows the evaluation of aroma with regard to Working examples 1 to 6 and Comparative example 1.
  • the perfume composition for incense stick is shown in Table 5. Also, the result of the evaluation of the smell quality in the sensing test is shown in Table 5, which was evaluated.
  • the evaluation standard is as follows. The evaluated values are average of 20 panels of specialist.
  • the perfume composition for the cosmetics is shown in Table 6.
  • the present inventors tried to add the fragrant wood extract for reproducing better agarwood fragrance.
  • the evaluation standard is as follows. The evaluated values are the average of 20 panels of specialist.
  • the evaluation standard is as follows. The evaluated values are the average of 20 panels of specialist.
  • the ratio of the fragrance collection liquid/the fragrant wood extract is preferably 0.25 to 9.
  • a method of collection of fragrance ingredient of the present invention comprises solvent extraction of an essential oil ingredient from a fragrant wood and collection of the fragrance ingredient in vapor-phase obtained by heating the extract. Accordingly, because the fragrance ingredient obtained has not burnt smell at all, it can be utilized as material for various uses. Only the fragrance part of the fragrant wood can be utilized fully. Namely, without being limited to conventional incense, incense stick etc., the application and the utilization of the wide area of perfume, cosmetics, aromatic etc. becomes possible.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Fats And Perfumes (AREA)
  • Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
  • Cosmetics (AREA)
US09/857,618 2000-05-31 2000-05-31 Method of collection of fragrance ingredient, perfume composition containing this fragrance ingredient and cosmetics containing this fragrance ingredient Expired - Fee Related US7001880B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/JP2000/003522 WO2000078117A2 (fr) 2000-05-31 2000-05-31 Procede permettant de se procurer un ingredient de fragrance, composition pour parfum et produits cosmetiques le contenant

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US7001880B1 true US7001880B1 (en) 2006-02-21

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US (1) US7001880B1 (fr)
EP (1) EP1127101B1 (fr)
JP (1) JP2003502482A (fr)
AU (1) AU5103600A (fr)
DE (1) DE60029923T2 (fr)
ES (1) ES2269149T3 (fr)
TW (1) TWI243686B (fr)
WO (1) WO2000078117A2 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103266015A (zh) * 2013-04-27 2013-08-28 中南林业科技大学 一种天然花香精油采集装置及使用方法
WO2017024072A1 (fr) * 2015-08-05 2017-02-09 Steele Casey Système et procédé d'extraction d'huiles essentielles
US10076714B1 (en) 2017-05-31 2018-09-18 Essential Innovations, Inc. Essential oil extraction, recovery, and purge method
CN111378526A (zh) * 2018-12-28 2020-07-07 贵州中烟工业有限责任公司 一种亚麻籽香精的制备方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6848211B2 (en) * 2001-05-24 2005-02-01 Regents Of The University Of Minnesota Cultivated agarwood
DE102006012866B4 (de) * 2006-03-19 2009-04-09 Uic Gmbh Verfahren zur Abtrennung leichtflüchtiger Komponenten aus einem Stoffgemisch sowie Vorrichtung zur Durchführung dieses Verfahrens
ITCS20130024A1 (it) * 2013-09-20 2015-03-20 Roberta Mandoliti Processo per la produzione di profumo di carta di libro.
EP3067409A1 (fr) * 2015-03-13 2016-09-14 Roberta Mandoliti Procédé pour la production de parfum de livre
CN104830528B (zh) * 2015-04-23 2018-05-18 东莞波顿香料有限公司 一种沉香香料的制备方法及使用方法
KR101769110B1 (ko) 2016-02-29 2017-08-17 전라남도 난대 산림수종의 산림욕 성분의 최적 추출 방법 및 그에 따라 제조된 난대 산림수종의 향기 추출물
CN107904017A (zh) * 2017-11-20 2018-04-13 杨敦阶 一种沉香精油制备工艺
IT201800005585A1 (it) * 2018-05-22 2019-11-22 Composti per prevenire e trattare affezioni della pelle o della mucosa con componente infiammatoria
KR102072191B1 (ko) * 2019-07-24 2020-01-31 김주현 크리스탈린 침향수의 제조방법
CN110585074B (zh) * 2019-10-22 2021-06-01 中国科学院兰州化学物理研究所 玫瑰精油香膏在化妆品中的应用
TWI693027B (zh) * 2019-10-28 2020-05-11 嘉藥學校財團法人嘉南藥理大學 氣味保存裝置
CN114606058A (zh) * 2020-12-08 2022-06-10 海南香树沉香产业集团股份有限公司 一种沉香芳香液的提取方法
AT525037B1 (de) * 2021-07-12 2022-12-15 Waldweihrauch Vom Bregahof E U Aromatisiertes Gemisch, sowie ein Verfahren und eine Vorrichtung zum Bereitstellen eines derartigen Gemisches
CN115433637A (zh) * 2022-09-29 2022-12-06 东莞市鸿馥生物科技有限公司 一种绿茶香料的制备方法

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103266015A (zh) * 2013-04-27 2013-08-28 中南林业科技大学 一种天然花香精油采集装置及使用方法
WO2017024072A1 (fr) * 2015-08-05 2017-02-09 Steele Casey Système et procédé d'extraction d'huiles essentielles
US10307690B2 (en) 2015-08-05 2019-06-04 Essential Innovations, Inc. Method for extracting essential oils
US10343082B2 (en) 2015-08-05 2019-07-09 Essential Innovations, Inc. System for extracting essential oils
US10076714B1 (en) 2017-05-31 2018-09-18 Essential Innovations, Inc. Essential oil extraction, recovery, and purge method
US10272361B2 (en) 2017-05-31 2019-04-30 Essential Innovations, Inc. Essential oil extraction, recovery, and purge system
US10293274B2 (en) 2017-05-31 2019-05-21 Essential Innovations, Inc. Essential oil extraction, recovery, and purge system and method
CN111378526A (zh) * 2018-12-28 2020-07-07 贵州中烟工业有限责任公司 一种亚麻籽香精的制备方法

Also Published As

Publication number Publication date
DE60029923T2 (de) 2007-08-30
WO2000078117A2 (fr) 2000-12-28
DE60029923D1 (de) 2006-09-21
EP1127101B1 (fr) 2006-08-09
TWI243686B (en) 2005-11-21
JP2003502482A (ja) 2003-01-21
ES2269149T3 (es) 2007-04-01
EP1127101A1 (fr) 2001-08-29
WO2000078117A3 (fr) 2001-05-25
AU5103600A (en) 2001-01-09

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